二萘[1,8‐bc: 1,8‐fg][1,5]二硫辛二亚胺( Dinaphtho[1,8‐bc:1 ,8 ‐fg][1,5]dithiocine Bisimide )

Y Tanaka K Tajima N Fukui H Shinokubo perylene bisimideV-shaped π-systemsulfurinversion dynamicsinsertion

V﹕haped π﹕ystems are attractive research targets in organic chemistry and materials science. Our group has recently demonstrated that the conceptual insertion of a heteroatom into a perylene bisimide (PBI) core is an effective guideline for the design of non﹑lanar PBI derivatives. Here we report the synthesis and properties of dinaphtho[1,8bc :1 ,8 fg ][1,5]dithiocine bisimide (DNDTBI), which represents a doubly sulfur﹊nserted PBI derivative. The X‐ray diffraction analysis revealed that DNDTBI adopted a V﹕haped structure with a dihedral angle of 67°. DNDTBI exhibited higher electronヾonating ability than singly sulfur﹊nserted PBI derivative owing to the antibonding interaction between the two neighboring sulfur atoms. The inversion barrier of the flipping motion of DNDTBI was ca. 30 kcal mol –1 , indicating the rigid nature of the V﹕haped structure.

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